Synthesis and stereochemistry of ω-azolylalkenes [1]

ω-Azolylalkenes 3, 4, and 5 were synthesized by N-alkylation of C-alkylation of ω-bromoalkenes 2, which were obtained either by phase transfer Wittig reactions of ω-bromoalkylphosphonium salts 1 with aldehydes or by Wittig reactions of ω-hydroxyalkylphosphonium salts 6 with aldehydes and subsequent bromination. ω-Azolylalkenes 3 were also directly prepared by the Wittig reaction of ω-azolylalkyltriphenylphosphonium salts 8 with aromatic aldehydes. The stereochemistry of these Wittig reactions was studied. © 1997 John Wiley & Sons, Inc.